TW414791B - Process and intermediates for preparing naphthyridonecarboxylic acid salts - Google Patents

Process and intermediates for preparing naphthyridonecarboxylic acid salts Download PDF

Info

Publication number: TW414791B
Authority: TW; Taiwan
Prior art keywords: compound; formula; scope; patent application; item
Prior art date: 1994-01-18

Application number

TW083111804A

Other languages

English (en)

Chinese (zh)

Inventor

Tamim F Braish

Darrell E Fox

Timothy Norris

Peter R Rose

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-01-18

Filing date

1994-12-17

Publication date

2000-12-11

1994-12-17 Application filed by Pfizer filed Critical Pfizer

2000-12-11 Application granted granted Critical

2000-12-11 Publication of TW414791B publication Critical patent/TW414791B/zh

Links

238000000034 method Methods 0.000 title claims abstract description 52
239000002253 acid Substances 0.000 title claims abstract description 41
239000000543 intermediate Substances 0.000 title abstract description 7
150000003839 salts Chemical class 0.000 title abstract 4
150000001875 compounds Chemical class 0.000 claims abstract description 120
-1 naphthyridone carboxylic acid Chemical class 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims description 24
238000011049 filling Methods 0.000 claims description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 13
239000002184 metal Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 12
239000003638 chemical reducing agent Substances 0.000 claims description 11
239000007789 gas Substances 0.000 claims description 10
230000002079 cooperative effect Effects 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000012380 dealkylating agent Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
229910052725 zinc Inorganic materials 0.000 claims description 5
239000011701 zinc Substances 0.000 claims description 5
229910052786 argon Inorganic materials 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
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DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 1
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238000002360 preparation method Methods 0.000 abstract description 5
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229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
238000007667 floating Methods 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000006166 lysate Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000007639 printing Methods 0.000 description 1
229960005335 propanol Drugs 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
YPPQYORGOMWNMX-UHFFFAOYSA-L sodium phosphonate pentahydrate Chemical class [Na+].[Na+].[O-]P([O-])=O YPPQYORGOMWNMX-UHFFFAOYSA-L 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
235000013555 soy sauce Nutrition 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW083111804A 1994-01-18 1994-12-17 Process and intermediates for preparing naphthyridonecarboxylic acid salts TW414791B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US18194294A	1994-01-18	1994-01-18

Publications (1)

Publication Number	Publication Date
TW414791B true TW414791B (en)	2000-12-11

Family

ID=22666458

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW083111804A TW414791B (en)	1994-01-18	1994-12-17	Process and intermediates for preparing naphthyridonecarboxylic acid salts

Country Status (19)

Country	Link
EP (1)	EP0740667A1 (fr)
JP (1)	JP2891543B2 (fr)
KR (1)	KR100221386B1 (fr)
CN (1)	CN1141634A (fr)
AU (1)	AU694149B2 (fr)
BR (1)	BR9408490A (fr)
CA (1)	CA2181351C (fr)
CZ (1)	CZ286896B6 (fr)
FI (1)	FI962880A7 (fr)
HU (1)	HUT74883A (fr)
IL (1)	IL112323A (fr)
MY (1)	MY130510A (fr)
NO (1)	NO305838B1 (fr)
NZ (1)	NZ276478A (fr)
PL (1)	PL179996B1 (fr)
RU (1)	RU2147303C1 (fr)
TW (1)	TW414791B (fr)
WO (1)	WO1995019361A1 (fr)
ZA (1)	ZA95340B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996039406A1 (fr) *	1995-06-06	1996-12-12	Pfizer Inc.	NOUVELLE FORME DE CRISTAL DE SEL ANHYDRE D'ACIDE METHANE-SULFONIQUE ET D'ACIDE 7-([1α, 5α, 6α]-6-AMINO-3-AZABICYCLO[3.1.0]HEX-3-YL)-6-FLUORO-1-(2,4-DIFLUOROPHENYL)-1,4-DIHYDRO-4-OXO-1,8-NAPHTYRIDINE-3 CARBOXYLIQUE
ES2095809B1 (es) *	1995-07-27	1997-12-16	Sint Quimica Sa	Procedimiento para la preparacion de acidos naftiridin carboxilicos y sus sales.
GB9524466D0 (en) *	1995-11-30	1996-01-31	Pfizer Ltd	Process
JPH1087617A (ja) *	1996-07-09	1998-04-07	Pfizer Inc	キノリン系抗生物質の合成に有用な中間体の製法
GB9614422D0 (en) *	1996-07-09	1996-09-04	Pfizer Ltd	Novel process
HN1998000106A (es)	1997-08-01	1999-01-08	Pfizer Prod Inc	Composiciones parenterales de alatroflaxacino
US6114531A (en) *	1998-07-28	2000-09-05	Pfizer Inc.	Process for preparing quinolone and naphthyridone carboxylic acids
HN1999000141A (es) *	1998-09-03	2000-06-19	Pfizer Prod Inc	Procedimiento para preparar sales de trovafloxacina de adicion de acidos.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5164402A (en) *	1989-08-16	1992-11-17	Pfizer Inc	Azabicyclo quinolone and naphthyridinone carboxylic acids
US5256791A (en)	1992-03-02	1993-10-26	Pfizer Inc.	Preparation of intermediates in the synthesis of quinoline antibiotics

1994
- 1994-12-12 EP EP95901569A patent/EP0740667A1/fr not_active Withdrawn
- 1994-12-12 NZ NZ276478A patent/NZ276478A/en unknown
- 1994-12-12 WO PCT/IB1994/000410 patent/WO1995019361A1/fr not_active Ceased
- 1994-12-12 CZ CZ19962111A patent/CZ286896B6/cs not_active IP Right Cessation
- 1994-12-12 PL PL94317043A patent/PL179996B1/pl unknown
- 1994-12-12 CN CN94194842A patent/CN1141634A/zh active Pending
- 1994-12-12 AU AU10754/95A patent/AU694149B2/en not_active Ceased
- 1994-12-12 HU HU9601957A patent/HUT74883A/hu unknown
- 1994-12-12 BR BR9408490A patent/BR9408490A/pt not_active Application Discontinuation
- 1994-12-12 KR KR1019960703846A patent/KR100221386B1/ko not_active Expired - Fee Related
- 1994-12-12 RU RU96115919A patent/RU2147303C1/ru active
- 1994-12-12 JP JP7518931A patent/JP2891543B2/ja not_active Expired - Lifetime
- 1994-12-12 CA CA002181351A patent/CA2181351C/fr not_active Expired - Fee Related
- 1994-12-17 TW TW083111804A patent/TW414791B/zh not_active IP Right Cessation
1995
- 1995-01-12 IL IL11232395A patent/IL112323A/en not_active IP Right Cessation
- 1995-01-17 ZA ZA95340A patent/ZA95340B/xx unknown
- 1995-01-17 MY MYPI95000103A patent/MY130510A/en unknown
1996
- 1996-07-17 FI FI962880A patent/FI962880A7/fi unknown
- 1996-07-17 NO NO962990A patent/NO305838B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR100221386B1 (ko)	1999-09-15
WO1995019361A1 (fr)	1995-07-20
BR9408490A (pt)	1997-08-26
AU1075495A (en)	1995-08-01
NO962990L (no)	1996-07-17
CA2181351C (fr)	1999-09-28
CN1141634A (zh)	1997-01-29
PL179996B1 (en)	2000-11-30
EP0740667A1 (fr)	1996-11-06
RU2147303C1 (ru)	2000-04-10
HU9601957D0 (en)	1996-09-30
FI962880A0 (fi)	1996-07-17
FI962880A7 (fi)	1996-07-17
JPH09501182A (ja)	1997-02-04
CA2181351A1 (fr)	1995-07-20
IL112323A (en)	2001-03-19
MY130510A (en)	2007-06-29
JP2891543B2 (ja)	1999-05-17
NO305838B1 (no)	1999-08-02
CZ286896B6 (en)	2000-07-12
PL317043A1 (en)	1997-03-03
ZA95340B (en)	1996-07-17
NZ276478A (en)	1998-05-27
AU694149B2 (en)	1998-07-16
CZ211196A3 (en)	1997-01-15
IL112323A0 (en)	1995-03-30
HUT74883A (en)	1997-02-28
NO962990D0 (no)	1996-07-17

Legal Events

Date	Code	Title	Description
2001-04-27	GD4A	Issue of patent certificate for granted invention patent
2002-11-11	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
KR100937915B1 (ko)	2010-01-21	변형된 픽텟-스펭글러 반응 및 그것으로부터 제조된생성물
US6184380B1 (en)	2001-02-06	Process for preparing naphthyridones and intermediates
CA3105786A1 (fr)	2020-01-16	Acide (r)-4-(1-(1-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamide)cyclopropyl)-benzoique en tant qu'antagoniste du recepteur ep4
HUT70048A (en)	1995-09-28	Neurotensine-receptor-active 1-naphtyl-pyrazol-3-carboxamides process for producing them and pharmaceutical compositions containing them as active components
TW414791B (en)	2000-12-11	Process and intermediates for preparing naphthyridonecarboxylic acid salts
CH633796A5 (fr)	1982-12-31	Dipyridoindoles therapeutiquement actifs.
TWI491607B (zh)	2015-07-11	４，４’-（１-甲基-１，２-乙二基）-雙-（２，６-哌二酮）之新製法
RU2222535C2 (ru)	2004-01-27	3-тетрагидропиридин-4-илиндолы для лечения психотических нарушений
JPH045289A (ja)	1992-01-09	アミド化合物
HU196798B (en)	1989-01-30	Process for producing quinazoline-diones and pyridopyrimidine-dions
JPS5833877B2 (ja)	1983-07-22	ユウキカゴウブツニカンスルカイリヨウ
HU191535B (en)	1987-03-30	Process for producing 2-azabicyclo/2.2.2/octane derivatives
TW318847B (fr)	1997-11-01
TW483890B (en)	2002-04-21	A process for preparing naphthyridones and intermediates
CA2227513C (fr)	2003-04-29	Nouveaux derives d'ellipticine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
AP1118A (en)	2002-11-21	Process for preparing trovafloxacin acid salts.
HUT74173A (en)	1996-11-28	Pyrido(1,2,3-de)quinoxaline derivatives, process for preparing the same and pharmaceutical compositions containing them
Gaikwad et al.	2022	Archive of SID. ir
Gaikwad et al.	2022	Journal of Medicinal and Chemical Sciences
JPH0480890B2 (fr)	1992-12-21
US20020095043A1 (en)	2002-07-18	Process for preparing naphthyridones and intermediates
CZ135397A3 (cs)	1998-05-13	Eficientní a vysoce enantiomerně selektivní způsob výroby enantiomerně čistých cyklopentan-ß-aminokyselin
KR100236818B1 (ko)	2000-03-15	나프티리돈카복실산 염의 중간체 및 그의 제조방법
CA1050021A (fr)	1979-03-06	Aza-6 3h-1 benzodiazepines-4
US20040019070A1 (en)	2004-01-29	Pyrrole-condensed morphinoid derivatives